2'-Deoxyadenosine monohydrate Chemical Properties

Melting point:

187-189 °C

refractive index 

-25.5 ° (C=0.5, H2O)

storage temp. 

2-8°C

solubility 

H2O: soluble50mg/mL, clear, colorless

form 

powder

color 

White to light beige

Water Solubility 

0.3 g/100 mL (20 ºC)

BRN 

5191174

Stability:

Stable, but air sensitive. Incompatible with strong oxidizing agents.

InChI

InChI=1/C10H13N5O3.H2O/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7;/h3-7,16-17H,1-2H2,(H2,11,12,13);1H2/t5-,6+,7+;/s3

InChIKey

WZJWHIMNXWKNTO-VWZUFWLJSA-N

SMILES

NC1=NC=NC2N([C@H]3C[C@H](O)[C@@H](CO)O3)C=NC1=2.O |&1:7,9,11,r|

CAS DataBase Reference

16373-93-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

24/25-37/39-36-26

RIDADR 

UN2811 6.1/PG 3

WGK Germany 

3

RTECS 

AU7358600

F 

10-23

TSCA 

Yes

HS Code 

29349990

MSDS

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2'-Deoxyadenosine monohydrate Usage And Synthesis

Description

2'-Deoxyadenosine monohydrate is an adenosine nucleotide, which can be synthesized by the enzyme adenosine kinase. 2'-Deoxyadenosine monohydrate is a competitive inhibitor of phosphodiesterase, which breaks down cyclic nucleotides to their corresponding monophosphate form. This leads to elevated levels of cAMP, which can cause neuronal death by apoptosis.

Chemical Properties

White crystalline powder

Uses

2'-Deoxyadenosineise is used by some cells as an energy source under energy stress conditions and to affect cAMP levels. 2'-dAdo is used in comparison studies of the functions of adenosine analogues on various biological processes.

Uses

2′-Deoxyadenosine monohydrate has been used:

• as a component for nucleoside supplementation
• as a standard for to estimate DNA global methylation rate in proliferating oil palm embryogenic suspensions
• to reverse sterile alpha motif (SAM) and histidine-aspartate (HD) domain-containing protein (SAMHD1)
• inhibition of human immunodeficiency virus (HIV-1) and hepatitis B virus (HBV)

Uses

2'-Deoxyadenosine monohydrate is used in the synthesis of 5'-modified 2'-deoxyadenosine analogues as anti-hepatitis C virus agents.

Biochem/physiol Actions

Excess 2′-deoxyadenosine gets converted to adenosine triphosphate (dATP), which inhibits ribonucleotide reductase.

Purification Methods

Purify it by recrystallisation from H2O (hydrated crystals; solubility of the monohydrate is 1.1% in H2O at 20o). It has max 258nm (pH 1), 260nm (pH 7) and 261nm (pH 13). [Ness & Fletcher J Am Chem Soc 81 4752 1959, Walker & Butler Can J Chem 34 1168 1956.] The 3',5'-O-diacetyl derivative has m 151-152o (from EtOAc/pet ether). [Beilstein 26 III/IV 3589.]

2'-Deoxyadenosine monohydrate(16373-93-6)Related Product Information

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